BONUS: Kailee's offer

New storyline involving Kailee Pound! Writing comes courtesy of the incredible Fred Key. Stay tuned for more!

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Chewing one end of a loose strand of hair, the girl read over the letter once more.

It was an unexpected letter.  When she had first seen it, the crisp, cream-colored envelope with the DIARY logo on it, her heart had leapt into her throat, and her hand had gone straight to her backside as if to protect it from some invisible, lurking, strap-wielding spanker.  She wouldn’t have even been embarrassed, she thought, if someone saw her do that, because EVERY teen in Puttsdale would react the same way.  Hell, most of the adults would, too!  I bet even Mandy Peabody would need a pair of Depends if she saw this envelope in her morning mail.

She winced as her hand brushed over a sore spot.  Fuck me! she thought, that hurts! The thought was quickly replaced by memories of just how the spanking that generated that pain had occurred, the substantial pleasure that had come with it, and a sudden interest in what a certain pair of people would be doing tonight.  Her hand slid inside the back of her cutoffs, under the panties beneath, and lightly caressed the welts she felt there.  “Fuck me!” she said with a laugh and a totally different inflection.  “Now there’s the best idea I’ve had since last night!”

She set the letter down on her bed, then unbuttoned her cutoffs and let them drop.  Turning her butt to the mirror, she looked back over her shoulder and pulled up one side of her panties to reveal a cheek with nice, even stripes that any child brought up in the town would instantly recognize as the work of a belt wielded by a practiced hand.  The angry red clashed with the green fabric, making her feel like a sideways stoplight was glaring at her.  She blew out a huff of air to get a hanging bit of hair out of her eyes, then sighed.

You’re acting like a thirteen year old staring at her fucking Harry Styles poster and rubbing one out.  Stop it.  You aren’t going to make a fool out of yourself over some guy.  At the same time, she knew that she was lying to herself. After last night, she’d probably do just about anything he wanted to try, and she had every intention of bratting her way into another wild night as soon as possible.  Maybe, she thought, she’d even invite her bestie again.

Kailee pulled her lime green undies back into place, and put her shorts back on.  She and Maggie had fooled around a bit before, and everyone knew Maggie was Maggie and that she was basically omnisexual, but Kailee had never imagined herself in a threesome, getting her ass whipped by her boyfriend and her best friend at the same time, wailing in pain and then in pleasure as both of them devoured her body afterwards, top and bottom and inside and outside and then oh my GAWD the incredible orgasm that had left her unable to speak.  She could only whimper as the quivers slowly died down as she was snuggled between her two bedmates.

She looked down at her hand, which had pulled out her phone to call him without her even thinking about it.  She realized where her other hand was, too, and blushed almost as pink as the streak in her hair this week.  I gotta take a cold shower or something.  Geez!

The letter.  What was she going to do?

She read it once more:

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May 29

Dear Ms. Pound,

As you no doubt know, D.I.A.R.Y. is a program which has a long tradition of changing lives.  We pride ourselves on the transformative nature of our school, and the way that we take raw young people with issues and turn them into future leaders who make our community proud.

This is not always an easy process.  D.I.A.R.Y. students are often youngsters who have proven themselves to be behaviorally challenged, or who make poor decisions.  They are sometimes unmotivated students, and sometimes just defiant for the sake of being defiant.  Some have broken so many rules that their parents have given them the choice - either enroll at D.I.A.R.Y. or leave home and make it on your own.  Our staff have to be patient, strong, and creative people in order to find the right methods to bring each student to our fullest potential.  We are proud to say that our previous director’s own daughter is a fine example of what D.I.A.R.Y. can achieve - a state championship winning swimmer with multiple scholarship offers and a fine sense of personal discipline.

As the new head of school, I fully intend to maintain this tradition of excellence.  However, as times change, we must change with them.  We must make sure that our staff include those who understand the minds of young adults.  Frankly, we need staff members who know what forms of discipline are most effective for the current generation, be they physical or psychological in nature.

To that end, I have established the E.D.I.T. program - Effective Disciplinarians In Training.  This program is designed to bring in promising candidates who have shown the creativity we think is necessary to develop solid punishment practices and who have the experience themselves to know what works and what doesn’t.  Principal Hawthorne recommended you as a young woman who has extensive experience with discipline, and who has, as he put it, “a surprisingly creative naughty streak.”

We would therefore like to offer you a trial position this summer as an intern in the E.D.I.T. program.  Your responsibilities would include supervision and discipline of students, including holding training sessions as needed for our established instructors to help them learn new and effective punishment methods.  Should you complete the internship program successfully, you may be offered a more permanent position on the D.I.A.R.Y. staff, or be provided with a college scholarship to help you obtain the necessary education to hold that position in the future.

Be advised, however, that interns are themselves subject to review by their superiors.  In the event that your work is found to be substandard, or should your supervisor determine that you have broken school policies, you will be subject to discipline yourself.  This is standard procedure for all of our employees, but you will be required to sign a waiver authorizing the school to punish you as it sees fit prior to employment.

I hope to hear from you soon regarding acceptance of this position.

Regards,

D.I.A.R.Y. Academy Staff Associates

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Kailee looked at the letter once more.  A tiny smile appeared on her face.  Well, it’s either this or back to Iggy’s for another summer…and if anyone knows punishments, it’s me!  Those kids have no idea what they’re in for…

She pulled out her phone and dialed the number at the bottom of the letter.   “Hello?  My name is Kailee Pound, and I’d like to speak to someone about an internship offer, please.”

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I'm so excited to start releasing the new Academy text adventure! Thank you so much to Fred Key for your help, and to all of my patrons for your support!